p-Dimethylaminocinnamaldehyde

p-Dimethylaminocinnamaldehyde (DMACA) is an aromatic hydrocarbon. It is used in an acidic solution to detect indoles.

p-Dimethylaminocinnamaldehyde
Names
IUPAC name
3-[4-(Dimethylamino)phenyl]prop-2-enal
Other names
DMAC
4-Dimethylaminocinnamaldehyde
Identifiers
3D model (JSmol)
Abbreviations DMACA
972369
ChemSpider
EC Number
  • 228-267-0
MeSH 4-Dimethylaminocinnamaldehyde
UNII
  • InChI=1S/C11H13NO/c1-12(2)11-7-5-10(6-8-11)4-3-9-13/h3-9H,1-2H3/b4-3+
    Key: RUKJCCIJLIMGEP-ONEGZZNKSA-N
  • InChI=1/C11H13NO/c1-12(2)11-7-5-10(6-8-11)4-3-9-13/h3-9H,1-2H3/b4-3+
    Key: RUKJCCIJLIMGEP-ONEGZZNKBZ
  • [H]C(=O)C=CC1=CC=C(C=C1)N(C)C
Properties
C11H13NO
Molar mass 175.22 g/mol
Appearance white to light yellow crystal powder
Density 1.057 g/mL
Melting point 138 °C (280 °F; 411 K)
Boiling point 329 °C (624 °F; 602 K)
Solubility in dioxane 50 g/L
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Use as a testing reagent

The DMACA is any of a number of acidified DMACA solutions:

  • 0.117 g of DMACA, 39 mL of ethanol, 5 mL of conc hydrochloric acid and diluted to 50mL with water[1]
  • 1 g DMACA, 1 mL conc. hydrochloric acid and 99 mL water[2]
  • 1 g DMACA in 99 mL conc. hydrochloric acid.[3]

It is primarily used as a histological dye used to detect indoles, particularly for production in cells. It is used for the rapid identification of bacteria containing tryptophanase enzyme systems. It is also particularly useful for localization of proanthocyanidins compounds in plants, resulting in a blue staining. It has been used for grapevine fruit[4] or for legumes foliage[5] histology.

A colorimetric assay based upon the reaction of A-rings with the chromogen. p-Dimethylaminocinnamaldehyde has been developed for flavanoids in beer that can be compared with the vanillin procedure.[6] The DMACA reagent may be superior to the vanillin procedure for the detection of catechins.[7]

The DMACA reagent changes color over several days when exposed to air but when refrigerated can be stored for up to two weeks.[8]

The DMACA reagent may also be referred to as the Renz and Loew reagent.[3][9]

See also

References
  1. Porubsky, P.; Scott, E.; Williams, T. (2008). "P-Dimethylaminocinnamaldehyde derivatization for colorimetric detection and HPLC–UV/vis–MS/MS identification of indoles". Archives of Biochemistry and Biophysics. 475 (1): 14–17. doi:10.1016/j.abb.2008.03.035. PMC 2504418. PMID 18423367.
  2. Sigma-Aldrich Co. LLC. "DMACA Reagent for microbiology". Retrieved 2013-10-29.
  3. Chung, K. R.; Shilts, T.; Ertürk, Ã. M.; Timmer, L. W.; Ueng, P. P. (2003). "Indole derivatives produced by the fungusColletotrichum acutatumcausing lime anthracnose and postbloom fruit drop of citrus". FEMS Microbiology Letters. 226 (1): 23–30. doi:10.1016/S0378-1097(03)00605-0. PMID 13129603.
  4. Bogs, J.; Jaffe, F. W.; Takos, A. M.; Walker, A. R.; Robinson, S. P. (2007). "The Grapevine Transcription Factor VvMYBPA1 Regulates Proanthocyanidin Synthesis during Fruit Development". Plant Physiology. 143 (3): 1347–1361. doi:10.1104/pp.106.093203. PMC 1820911. PMID 17208963.
  5. Li, Y. G.; Tanner, G.; Larkin, P. (1996). "TheDMACA-HCl Protocol and the Threshold Proanthocyanidin Content for Bloat Safety in Forage Legumes". Journal of the Science of Food and Agriculture. 70: 89–101. doi:10.1002/(SICI)1097-0010(199601)70:1<89::AID-JSFA470>3.0.CO;2-N.
  6. A new colourimetric assay for flavonoids in pilsner beers. Jan A. Delcour and Didier Janssens de Varebeke, Journal of the Institute of Brewing, January–February 1985, Volume 91, Issue 1, pages 37–40, doi:10.1002/j.2050-0416.1985.tb04303.x
  7. Glavnik, V.; Simonovska, B.; Vovk, I. (2009). "Densitometric determination of (+)-catechin and (−)-epicatechin by 4-dimethylaminocinnamaldehyde reagent". Journal of Chromatography A. 1216 (20): 4485–91. doi:10.1016/j.chroma.2009.03.026. PMID 19339019.
  8. Meudt, W. J.; Gaines, T. P. (1967). "Studies on the Oxidation of Indole-3-Acetic Acid by Peroxidase Enzymes. I. Colorimetric Determination of Indole-3-Acetic Acid Oxidation Products". Plant Physiology. 42 (10): 1395–9. doi:10.1104/pp.42.10.1395. PMC 1086736. PMID 16656668.
  9. Ehmann, A. (1977). "The van URK-Salkowski reagent — a sensitive and specific chromogenic reagent for silica gel thin-layer chromatographic detection and identification of indole derivatives" (PDF). Journal of Chromatography A. 132 (2): 267–276. doi:10.1016/S0021-9673(00)89300-0. PMID 188858.
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